JPH0233696B2 - SHIANOSHIKUROHEKISANJUDOTAI - Google Patents
SHIANOSHIKUROHEKISANJUDOTAIInfo
- Publication number
- JPH0233696B2 JPH0233696B2 JP23456082A JP23456082A JPH0233696B2 JP H0233696 B2 JPH0233696 B2 JP H0233696B2 JP 23456082 A JP23456082 A JP 23456082A JP 23456082 A JP23456082 A JP 23456082A JP H0233696 B2 JPH0233696 B2 JP H0233696B2
- Authority
- JP
- Japan
- Prior art keywords
- trans
- liquid crystal
- phenyl
- point
- pentylcyclohexyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 239000004973 liquid crystal related substance Substances 0.000 claims description 28
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- VBWIZSYFQSOUFQ-UHFFFAOYSA-N cyclohexanecarbonitrile Chemical compound N#CC1CCCCC1 VBWIZSYFQSOUFQ-UHFFFAOYSA-N 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 9
- 239000000463 material Substances 0.000 description 8
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
- NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
- NNJMFJSKMRYHSR-UHFFFAOYSA-N 4-phenylbenzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=CC=C1 NNJMFJSKMRYHSR-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- VZFUCHSFHOYXIS-UHFFFAOYSA-N cycloheptane carboxylic acid Natural products OC(=O)C1CCCCCC1 VZFUCHSFHOYXIS-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- -1 trans-4- [4′-(trans-4′′-pentylcyclohexyl)phenyl]cyanocyclohexane Chemical compound 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- XXUSEPRYHRDKFV-CTYIDZIISA-N C1C[C@@H](CCC)CC[C@@H]1C1=CC=C(C#N)C=C1 Chemical compound C1C[C@@H](CCC)CC[C@@H]1C1=CC=C(C#N)C=C1 XXUSEPRYHRDKFV-CTYIDZIISA-N 0.000 description 1
- FURZYCFZFBYJBT-JCNLHEQBSA-N C1C[C@@H](CCCCC)CC[C@@H]1C1=CC=C(C#N)C=C1 Chemical compound C1C[C@@H](CCCCC)CC[C@@H]1C1=CC=C(C#N)C=C1 FURZYCFZFBYJBT-JCNLHEQBSA-N 0.000 description 1
- GLVQBAYHWDUEQI-YKFMMLSNSA-N C1C[C@@H](CCCCC)CC[C@@H]1C1=CC=C([C@@H]2CC[C@H](CC2)C(O)=O)C=C1 Chemical compound C1C[C@@H](CCCCC)CC[C@@H]1C1=CC=C([C@@H]2CC[C@H](CC2)C(O)=O)C=C1 GLVQBAYHWDUEQI-YKFMMLSNSA-N 0.000 description 1
- NSGMZTNTQKRAFA-UAPYVXQJSA-N C1C[C@@H](CCCCCCC)CC[C@@H]1C1=CC=C(C#N)C=C1 Chemical compound C1C[C@@H](CCCCCCC)CC[C@@H]1C1=CC=C(C#N)C=C1 NSGMZTNTQKRAFA-UAPYVXQJSA-N 0.000 description 1
- 239000004986 Cholesteric liquid crystals (ChLC) Substances 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 239000004988 Nematic liquid crystal Substances 0.000 description 1
- 239000004990 Smectic liquid crystal Substances 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000007333 cyanation reaction Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Liquid Crystal Substances (AREA)
Description
【発明の詳細な説明】
本発明は広い温度で液晶相を示す、正の誘電異
方性を有する新規液晶物質及びそれを含有する液
晶組成物に関する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a novel liquid crystal material exhibiting a liquid crystal phase over a wide range of temperatures and having positive dielectric anisotropy, and a liquid crystal composition containing the same.
液晶を使用した表示素子は時計、電卓などに広
く使用される様になつて来た。この液晶表示素子
は液晶物質の光学異方性及び誘電異方性という性
質を利用したものであるが、液晶相にはネマチツ
ク液晶相、スメクチツク液晶相、コレステリツク
液晶相があり、そのうちネマチツク液晶を利用し
たものが最も広く実用化されている。更にそれら
にはTN（ねじれネマチツク）型、DS型（動的散
乱型）、ゲスト・ホスト型、DAP型などがあり、
それぞれに使用される液晶物質に要求される性質
は異る。しかし、いずれにしても、これら表示素
子に使用される液晶物質は自然界のなるべく広い
温度で液晶相を示すものが望ましいが、現在のと
ころ単一物質でその様な条件をみたす様な物質は
なく、数種の液晶物質又は非液晶物質を混合して
一応実用に耐える様な物を得ているのが現状であ
る。又、これらの物質は水分、光、熱、空気等に
対しても安定でなければならないのは勿論であ
り、更に表示素子を駆動させる必要なしきい電
圧、飽和電圧がなるべく低いこと、又応答速度を
早くするためには粘度が出来るだけ低いことが望
ましい。ところで液晶温度範囲を高温の方に広く
するためには高融点の液晶物質を成分として使用
する必要があるが、一般に高融点の液晶物質は粘
度が高く、従つてそれを含む液晶組成物も粘度が
高くなるので、高温、例えば80℃位まで使用出来
る様な液晶表示素子の応答速度、特に低温でのそ
れは著るしくおそくなる傾向にあつた。しかるに
本発明者らは高い液晶−透明点（Ｎ−Ｉ点）及び
広いネマチツク温度範囲をもちながら低粘度の液
晶物質を見つけ本発明に到つた。 Display elements using liquid crystals have come to be widely used in watches, calculators, etc. This liquid crystal display element utilizes the properties of optical anisotropy and dielectric anisotropy of liquid crystal materials, and there are three liquid crystal phases: nematic liquid crystal phase, smectic liquid crystal phase, and cholesteric liquid crystal phase. The one that has been put into practical use is the most widely used. Furthermore, they include TN (twisted nematic) type, DS (dynamic scattering type), guest-host type, DAP type, etc.
The properties required for the liquid crystal materials used in each case are different. However, in any case, it is desirable that the liquid crystal materials used in these display elements exhibit a liquid crystal phase over as wide a range of natural temperatures as possible, but there is currently no single material that satisfies these conditions. Currently, materials that can be put to practical use are obtained by mixing several types of liquid crystal substances or non-liquid crystal substances. In addition, these materials must of course be stable against moisture, light, heat, air, etc., and the threshold voltage and saturation voltage necessary to drive the display element must be as low as possible, and the response speed must be as low as possible. In order to speed up the process, it is desirable that the viscosity be as low as possible. By the way, in order to widen the liquid crystal temperature range toward higher temperatures, it is necessary to use a liquid crystal substance with a high melting point as a component, but liquid crystal substances with a high melting point generally have a high viscosity, and therefore the liquid crystal composition containing it also has a high viscosity. As the temperature increases, the response speed of liquid crystal display elements that can be used at high temperatures, for example, up to about 80° C., particularly at low temperatures, tends to become significantly slower. However, the present inventors have discovered a low viscosity liquid crystal material having a high liquid crystal clearing point (N-I point) and a wide nematic temperature range, and have arrived at the present invention.
即ち本発明は一般式
（上式中Ｒは炭素数１〜10のアルキル基を示す）
で表わされるトランス−４−〔4′−（トランス−
4″−アルキルシクロヘキシル）フエニル〕シアノ
シクロヘキサン及びそれを含有する液晶組成物で
ある。 That is, the present invention is based on the general formula (In the above formula, R represents an alkyl group having 1 to 10 carbon atoms) trans-4-[4'-(trans-
4″-Alkylcyclohexyl)phenyl]cyanocyclohexane and a liquid crystal composition containing the same.
本発明の化合物は高い透明点を有し、例えば本
発明の化合物の一つであるトランス−４−〔4′−
（トランス−4″−ペンチルシクロヘキシル）フエ
ニル〕シアノシクロヘキサンのＣ−Ｎ点は123.1
℃、Ｎ−Ｉ点は181.1℃と広い温度範囲で液晶相
を示し、これを液晶組成物の１成分として加える
ことによりその液晶組成物の粘度を高くせずに透
明点を上げることが出来る。又本発明の化合物の
誘電異方性値は＋１程度であるが、組成物のしき
い値電圧、飽和電圧をそれほど変化させない。又
水分、熱、光等に対する安定性も良好である。又
本発明化合物の光学異方性値Δnが小さく、その
性質を生かした表示用セルへ応用される。 The compounds of the present invention have a high clearing point, for example, one of the compounds of the present invention, trans-4-[4'-
The C-N point of (trans-4″-pentylcyclohexyl)phenyl]cyanocyclohexane is 123.1
C., N-I point is 181.1 DEG C., which shows a liquid crystal phase over a wide temperature range, and by adding it as a component to a liquid crystal composition, the clearing point can be raised without increasing the viscosity of the liquid crystal composition. Further, although the dielectric anisotropy value of the compound of the present invention is about +1, it does not change the threshold voltage and saturation voltage of the composition so much. It also has good stability against moisture, heat, light, etc. Further, the optical anisotropy value Δn of the compound of the present invention is small, and it can be applied to display cells that take advantage of this property.
次に本発明の化合物の製造法を示す。まず4′−
（トランス−4″−アルキルシクロヘキシル）ジフ
エニル−４−カルボン酸をイソアミルアルコール
中、金属ナトリウムで還元してトランス−４−
〔4′−（トランス−4″−アルキルシクロヘキシル）
フエニル〕シクロヘキサンカルボン酸を得る。次
いでこれを塩化チオニルで酸クロリドとした後、
アンモニアをを反応させて酸アミドとし、それを
塩化チオニルで脱水反応をして目的のトランス−
４−〔4′−（トランス−4″−アルキルシクロヘキシ
ル）フエニル〕シアノシクロヘキサンを製造し
た。 Next, a method for producing the compound of the present invention will be described. First 4′−
(trans-4″-alkylcyclohexyl)diphenyl-4-carboxylic acid was reduced with metallic sodium in isoamyl alcohol to obtain trans-4-
[4′-(trans-4″-alkylcyclohexyl)
phenyl]cyclohexanecarboxylic acid is obtained. Then, after converting this into acid chloride with thionyl chloride,
Ammonia is reacted to form an acid amide, which is then dehydrated with thionyl chloride to obtain the desired trans-
4-[4'-(trans-4''-alkylcyclohexyl)phenyl]cyanocyclohexane was produced.
以上を化学式で示すと、
以下実施例により本発明を更に詳細に説明す
る。 If the above is expressed as a chemical formula, The present invention will be explained in more detail with reference to Examples below.
実施例 １
〔トランス−４−〔4′−（トランス−４−ペンチ
ルシクロヘキシル）フエニル〕シアノシクロヘ
キシルの製造〕
(1) トランス−４−〔4′−（トランス−4″−ペンチ
ルシクロヘキシル）フエニル〕シクロヘキサン
カルボン酸の製造
4′−（トランス−4″−ペンチルシクロヘキシ
ル）ビフエニル−４−カルボン酸10ｇをイソア
ミルアルコール2500mlと共に撹拌し、90℃まで
加熱する。金属ナトリウム30ｇを加えると激し
く反応しはじめる。そのまま還流をつづけなが
ら３時間で金属ナトリウムを更に120ｇ加える
と反応液はしだいに均一になる。反応終了後、
放冷して100℃にする。次に水を加えながらイ
ソアミルアルコールを留去する。水は2000ml加
えた。次いで6N塩酸を２加え完全に酸性に
する。析出した沈澱を過、水洗する。更に酢
酸で再結晶してトランス−４−〔4′−トランス
−4″−ペンチルシクロヘキシル）フエニル〕シ
クロヘキサンカルボン酸4.5ｇを得た。このカ
ルボン酸も液晶性を示しそのＣ−Ｓ点は239.1
℃、Ｓ−Ｉ点は274.3℃（分解）。Example 1 [Production of trans-4-[4′-(trans-4-pentylcyclohexyl)phenyl]cyanocyclohexyl] (1) Trans-4-[4′-(trans-4″-pentylcyclohexyl)phenyl]cyclohexane Preparation of carboxylic acid 10 g of 4'-(trans-4''-pentylcyclohexyl)biphenyl-4-carboxylic acid are stirred with 2500 ml of isoamyl alcohol and heated to 90°C. When 30g of metallic sodium is added, a violent reaction begins. While continuing to reflux, an additional 120 g of metallic sodium was added over 3 hours, and the reaction solution gradually became homogeneous. After the reaction is complete,
Leave to cool to 100℃. Next, isoamyl alcohol is distilled off while adding water. Added 2000ml of water. Next, add 2 portions of 6N hydrochloric acid to make it completely acidic. The precipitate that has separated out is filtered and washed with water. Further recrystallization from acetic acid yielded 4.5 g of trans-4-[4'-trans-4''-pentylcyclohexyl)phenyl]cyclohexanecarboxylic acid. This carboxylic acid also exhibited liquid crystallinity and its C-S point was 239.1.
℃, S-I point is 274.3℃ (decomposition).
(2) シアノ化
(1)で製造したトランス−４−〔4′−（トランス
−4″−ペンチルシクロヘキシル）フエニル〕シ
クロヘキサンカルボン酸１ｇを塩化チオニル30
mlと共に80℃に加熱する。反応液は２時間で均
一になり、更に1.5時間反応をつづける。過剰
の塩化チオニルを減圧にて留去する。残つた油
状物は酸塩化物である。この油状物を100mlの
濃アンモニア水に激しく撹拌しながら加える。
１時間撹拌した後、生じた沈澱を過する。固
形物を風乾し、全量をフラスコに入れ塩化チオ
ニル100mlと共に加熱還流する。４〜５時間で
ほとんど均一になる。ついで過剰の塩化チオニ
ルを減圧で留去する。残つた油状物をトルエン
100mlに溶かし、トルエン層を2N−NaOHで３
回洗い、中性になるまで水で洗う。無水硫酸ナ
トリウムで乾燥後、活性アルミナのカラムを通
す。溶出液を濃縮後、残つた油状物をエタノー
ルで２回再結晶して目的のトランス−４−
〔4′−（トランス−4″−ペンチルシクロヘキシ
ル）フエニル〕シアノシクロヘキサンを得た。
収量0.2ｇ、収率21％。そのＣ−Ｎ点は123.1〜
124.8℃、Ｎ−Ｉ点は181.1℃であつた。又この
化合物が目的物であることは赤外線吸収スペク
トル及びNMRで確認した。(2) Cyanation 1 g of trans-4-[4′-(trans-4″-pentylcyclohexyl)phenyl]cyclohexanecarboxylic acid produced in (1) was converted to 30% thionyl chloride.
Heat to 80 °C with ml. The reaction solution became homogeneous in 2 hours, and the reaction was continued for an additional 1.5 hours. Excess thionyl chloride is distilled off under reduced pressure. The oil that remains is the acid chloride. Add this oil to 100 ml of concentrated aqueous ammonia with vigorous stirring.
After stirring for 1 hour, filter the resulting precipitate. The solid is air-dried, and the entire amount is placed in a flask and heated to reflux with 100 ml of thionyl chloride. It becomes almost uniform in 4 to 5 hours. Excess thionyl chloride is then distilled off under reduced pressure. Pour the remaining oily substance into toluene.
Dissolve in 100ml and dilute the toluene layer with 2N-NaOH.
Wash twice and with water until neutral. After drying with anhydrous sodium sulfate, it is passed through an activated alumina column. After concentrating the eluate, the remaining oil was recrystallized twice with ethanol to obtain the desired trans-4-
[4′-(trans-4″-pentylcyclohexyl)phenyl]cyanocyclohexane was obtained.
Yield 0.2g, yield 21%. Its C-N point is 123.1 ~
The temperature was 124.8°C, and the N-I point was 181.1°C. Furthermore, it was confirmed by infrared absorption spectrum and NMR that this compound was the target compound.
他のアルキル基を有する（）式の化合物
も、出発物質のカルボン酸として最終目的物に
対応するアルキル基をもつたものを使用する以
外は上記と同様にして得ることができる。 Compounds of the formula () having other alkyl groups can also be obtained in the same manner as above, except that a carboxylic acid having an alkyl group corresponding to the final target compound is used as the starting carboxylic acid.
実施例 ２（使用例）
トランス−４−プロピル−（4′−シアノフエニ
ル）シクロヘキサン 28％
トランス−４−ペンチル−（4′−シアノフエニ
ル）シクロヘキサン 42％
トランス−４−ヘプチル−（4′−シアノフエニ
ル）シクロヘキサン 30％
なる組成の液晶組成物のＮ−Ｉ点は52℃である。
この液晶組成物をセル厚10μｍのTNセル（ねじ
れネマチツクセル）に封入したもののしきい値電
圧は1.53V、飽和電圧は2.12Vであつた。又粘度
は20℃で23cp.光学異方性値は0.120であつた。Example 2 (Usage example) Trans-4-propyl-(4'-cyanophenyl)cyclohexane 28% Trans-4-pentyl-(4'-cyanophenyl)cyclohexane 42% Trans-4-heptyl-(4'-cyanophenyl)cyclohexane The N-I point of a liquid crystal composition having a composition of 30% is 52°C.
When this liquid crystal composition was sealed in a TN cell (twisted nematic cell) with a cell thickness of 10 μm, the threshold voltage was 1.53V and the saturation voltage was 2.12V. The viscosity was 23 cp at 20°C. The optical anisotropy value was 0.120.
この液晶組成物90部に実施例１で製造したトラ
ンス−４−〔4′−（トランス−4″−ペンチルシクロ
ヘキシル）フエニル〕シアノシクロヘキサン10部
を加えた液晶組成物のＮ−Ｉ点は63℃に上がつ
た。前記と同様にして測定したしきい値電圧は
1.55V、飽和電圧は2.14Vであつた。又粘度は20
℃で24cp.光学異方性値は0.120と殆んど変らなか
つた。 The N-I point of the liquid crystal composition obtained by adding 10 parts of trans-4-[4'-(trans-4''-pentylcyclohexyl)phenyl]cyanocyclohexane prepared in Example 1 to 90 parts of this liquid crystal composition was 63°C. The threshold voltage measured in the same manner as above was
The voltage was 1.55V, and the saturation voltage was 2.14V. Also, the viscosity is 20
℃ at 24cp.The optical anisotropy value was 0.120, which was almost unchanged.
Claims (1)
4″−アルキルシクロヘキシル）フエニル〕シアノ
シクロヘキサン。 ２ 一般式 （上式中Ｒは炭素数１〜10のアルキル基を示す） で表わされるトランス−４−〔4′−（トランス−
4″−アルキルシクロヘキシル）フエニル〕シアノ
シクロヘキサンを少くとも一種含有することを特
徴とする液晶組成物。[Claims] 1. General formula (In the above formula, R represents an alkyl group having 1 to 10 carbon atoms) trans-4-[4'-(trans-
4″-Alkylcyclohexyl)phenylcyanocyclohexane. 2 General formula (In the above formula, R represents an alkyl group having 1 to 10 carbon atoms) trans-4-[4'-(trans-
A liquid crystal composition containing at least one type of 4″-alkylcyclohexyl)phenyl]cyanocyclohexane.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP23456082A JPH0233696B2 (en) | 1982-12-25 | 1982-12-25 | SHIANOSHIKUROHEKISANJUDOTAI |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP23456082A JPH0233696B2 (en) | 1982-12-25 | 1982-12-25 | SHIANOSHIKUROHEKISANJUDOTAI |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS59118752A JPS59118752A (en) | 1984-07-09 |
| JPH0233696B2 true JPH0233696B2 (en) | 1990-07-30 |
Family
ID=16972925
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP23456082A Expired - Lifetime JPH0233696B2 (en) | 1982-12-25 | 1982-12-25 | SHIANOSHIKUROHEKISANJUDOTAI |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0233696B2 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH07241255A (en) * | 1991-03-28 | 1995-09-19 | Yasumichi Horinouchi | Unit device with built-in pedal type opening/closing mechanism for western style stool |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3158623B2 (en) * | 1992-04-03 | 2001-04-23 | チッソ株式会社 | Diene derivatives |
-
1982
- 1982-12-25 JP JP23456082A patent/JPH0233696B2/en not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH07241255A (en) * | 1991-03-28 | 1995-09-19 | Yasumichi Horinouchi | Unit device with built-in pedal type opening/closing mechanism for western style stool |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS59118752A (en) | 1984-07-09 |
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